Potassium Phosphate, Tribasic → HCID 89721854, compound

HRID 2273086Notes

Reaction equation

HRID 2273086 reaction equation
[CH2:1]([N:3]1[CH2:9][C:8]([CH3:11])([CH3:10])[O:7][C:6]2[N:12]=[C:13]([N:24]3[CH2:29][CH2:28][O:27][CH2:26][C@@H:25]3[CH3:30])[N:14]=[C:15](OS(C(F)(F)F)(=O)=O)[C:5]=2[C:4]1=[O:31])[CH3:2].[C:32]([O:36][C:37](=[O:55])[NH:38][C:39]1[CH:44]=[CH:43][C:42](B2OC(C)(C)C(C)(C)O2)=[CH:41][C:40]=1[CH3:54])([CH3:35])([CH3:34])[CH3:33].P([O-])([O-])([O-])=O.[K+].[K+].[K+]>O1CCOCC1.O.C(OCC)(=O)C.Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1>[C:32]([O:36][C:37](=[O:55])[NH:38][C:39]1[CH:44]=[CH:43][C:42]([C:15]2[C:5]3[C:4](=[O:31])[N:3]([CH2:1][CH3:2])[CH2:9][C:8]([CH3:11])([CH3:10])[O:7][C:6]=3[N:12]=[C:13]([N:24]3[CH2:29][CH2:28][O:27][CH2:26][C@@H:25]3[CH3:30])[N:14]=2)=[CH:41][C:40]=1[CH3:54])([CH3:33])([CH3:34])[CH3:35]

Participants

8

Reactant 3

HCID 62657Potassium Phosphate, TribasicHCID 53217256tert-Butyl [2-methyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]carbamateHCID 89714687HCID 89714687, compound

Product 1

HCID 89721854HCID 89721854, compoundYield 110.8%

Reagents, catalysts & solvents 4

HCID 178418476HCID 178418476, compoundCatalystHCID 962WaterSolventHCID 8857Ethyl AcetateSolventHCID 312751,4-DioxaneSolvent

Conditions

Temperature
100 °C

Procedure

A mixture of 1 g (2.13 mmol) of trifluoromethanesulfonic acid 6-ethyl-8,8-dimethyl-2-((S)-3-methylmorpholin-4-yl)-5-oxo-5,6,7,8-tetrahydro-9-oxa-1,3,6-triazabenzocyclohepten-4-yl ester, 711.35 mg (2.13 mmol) of [2-methyl-4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)phenyl]carbamic acid tert-butyl ester, 906.25 mg (4.27 mmol) of tribasic potassium phosphate, 149.83 mg (213.47 μmol) of bis(triphenylphosphine)palladium(II) chloride in 10 ml of dioxane and 3 ml of water is heated in a Biotage microwave machine at 100° C. for 30 minutes. The reaction medium is diluted in 250 ml of ethyl acetate and filtered through Celite. The organic phase is dried over MgSO4. The filtrate is evaporated under reduced pressure. The residue is taken up in 30 ml of heptane, brought to reflux and filtered while hot to give 1.24 g of {4-[6-ethyl-8,8-dimethyl-2-((S)-3-methylmorpholin-4-yl)-5-oxo-5,6,7,8-tetrahydro-9-oxa-1,3,6-triaza benzocyclohepten-4-yl]-2-methylphenyl}carbamic acid tert-butyl ester.

Workup

  1. filtrationfiltered through Celite
  2. dry with materialThe organic phase is dried over MgSO4
  3. customThe filtrate is evaporated under reduced pressure
  4. temperatureto reflux
  5. filtrationfiltered while hot

Sources & evidence

ORD record
ord-f49fbf915c4440c987ff1482d3baf9e6
Source dataset
uspto-grants-2015_09
Patent number
US09120812B2

Reaction notes

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